Roy OrbisonOh, snap, we picked Roy Orbison over Elton John! That’s because Elton John’s glasses are often not cool, while Orbison’s always were.

John LennonOK, we still kind of hate the round lenses, but the dude
certainly had a look. Ringo, by the way, has terrible taste in
spectacles.

Kool Moe DeeHonorable hip-hop shout-outs should go to D.M.C, Heavy D,
DJ Jazzy Jeff, and E-40 and company, but Kool Moe Dee had the best
shades ever. And, yes, we just referred to the man as a “musical
genius.” Knowledge is king!